O-((2E)-3-Chloro-2-propen-1-yl)hydroxylamine → HCID 178458081, compound

HRID 1606867Notes

Reaction equation

HRID 1606867 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]2[CH2:12][C:11](=[O:13])[CH:10]([C:14](=O)[CH2:15][CH3:16])[C:9](=[O:18])[CH2:8]2)[C:4]([CH3:19])=[N:3]1.[Cl:20]/[CH:21]=[CH:22]/[CH2:23][O:24][NH2:25]>C(O)C>[Cl:20][CH:21]=[CH:22][CH2:23][O:24]/[N:25]=[C:14](/[CH:10]1[C:11](=[O:13])[CH2:12][CH:7]([C:5]2[C:4]([CH3:19])=[N:3][N:2]([CH3:1])[CH:6]=2)[CH2:8][C:9]1=[O:18])\[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 158058O-((2E)-3-Chloro-2-propen-1-yl)hydroxylamineHCID 145764925-(1,3-dimethyl-1H-pyrazol-4-yl)-2-propionylcyclohexane-1,3-dione

Product 1

HCID 178458081HCID 178458081, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethanol was dissolved 2.62 g (10 mmols) of 5-(1,3-dimethyl-1H-pyrazol-4-yl)-2-propionylcyclohexane-1,3-dione and, 30 ml (12 mmols) of 0.4 mol ethanolic solution of (E)-3-chloro-2-propenyloxyamine was added to the solution. The mixture was reacted for 8 hours with stirring. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform:methanol=50:1) to give 3.21 g of the product.

Workup

  1. additionwas added to the solution
  2. customThe mixture was reacted for 8 hours
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-121bcdd4e0614e8f9b421f918e270746
Source dataset
uspto-grants-1989_09
Patent number
US04863504

Reaction notes

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